605-94-7Relevant articles and documents
A convenient two-step synthesis of Coenzyme Q1
Lu, Bin,Qiu, Yong-Fu,Qi, Shi,Wang, Jin
, p. 553 - 556 (2019)
A convenient method for the preparation of Coenzyme Q1 from cheap and readily available 3,4,5-trimethoxytoluene is developed. Coenzyme Q1 is synthesized in a moderate yield by a two-step procedure involving the key reaction of an allyl bromide with Coenzyme Q0 through a redox chain reaction. The reaction is efficient and can be used for the synthesis of other Coenzyme Q compounds.
Polyoxometalate-based supramolecular porous frameworks with dual-active centers towards highly efficient synthesis of functionalized: P -benzoquinones
An, Haiyan,Chang, Shenzhen,Chen, Yanhong,Huang, Yaohui,Luo, Huiyun,Zhu, Qingshan
, p. 8591 - 8603 (2021/11/17)
Selective oxidation of substituted phenols is an ideal method for preparing functionalized p-benzoquinones (p-BQs), which serve as versatile raw materials for the synthesis of a variety of biologically active compounds. Herein, two new polyoxometalate-based supramolecular porous frameworks, K3(H2O)4[Cu(tza)2(H2O)]2[Cu(Htza)2(H2O)2][BW12O40]·6H2O (1) and H3K3(H2O)3[Cu(Htza)2(H2O)]3[SiW12O44]·14H2O (2) (Htza = tetrazol-1-ylacetic acid), were synthesized and structurally characterized by elemental analysis, infrared spectroscopy, thermal analysis, UV-vis diffuse reflectance spectroscopy, and single-crystal X-ray and powder diffraction. The single-crystal X-ray diffraction analysis indicates that both compounds possess unique petal-like twelve-nucleated Cu-organic units composed of triangular and hexagonal metal-organic loops. In 1, the Cu-organic units are isolated and [BW12O40]5- polyoxoanions are sandwiched between staggered adjacent triangular channels in the structure. However in 2, the Cu-organic units extend into a two-dimensional layered structure, and the [SiW12O44]12- polyoxoanions occupy the larger hexagonal channels in the stacked structure. Both compounds as heterogeneous catalysts can catalyze the selective oxidation of substituted phenols to high value-added p-BQs under mild conditions (60 °C) with TBHP as the oxidant, particularly in the oxidation of 2,3,6-trimethylphenol to 2,3,5-trimethyl-p-benzoquinone (TMBQ, key intermediate in vitamin E production). Within 8-10 min, the yield of TMBQ is close to 100%, and oxidant utilization efficiency is up to 94.2% for 1 and 90.9% for 2. The turnover frequencies of 1 and 2 are as high as 5000 and 4000 h-1, respectively. No obvious decrease in the yield of TMBQ was observed after five cycles, which indicates the excellent sustainability of both compounds. Our study of the catalytic mechanism suggests that there is a two-site synergetic effect: (i) the copper ion acts as the catalytic site of the homolytic radical pathway; and (ii) the polyoxoanion acts as the active center of the heterolytic oxygen atom transfer pathway. This journal is
Coenzyme Q compound synthesis method
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Paragraph 0025-0032, (2020/11/01)
The invention relates to a coenzyme Q compound synthesis method, which comprises the steps of: dissolving substituted or unsubstituted 3, 4, 5-trimethoxytoluene in an organic solvent, carrying out a reaction on the obtained solution and an oxidant aqueous solution for 1-2h at a temperature of 20-80 DEG C under the catalysis of an acid, and carrying out extraction, water washing, reduced pressure distillation and recrystallization on the obtained crude product to obtain a coenzyme Q compound. Raw materials used in the method are cheap and easy to obtain, and no toxic or harmful waste gas or waste residue is generated in the reaction process; and reaction steps are few, the operation is easy and convenient, the product yield is high, and the method is suitable for industrial large-scale production.
Regiodivergent oxidation of alkoxyarenes by hypervalent iodine/oxone system
China, Hideyasu,Tanihara, Kokoro,Sasa, Hirotaka,Kikushima, Kotaro,Dohi, Toshifumi
, p. 2 - 8 (2019/09/10)
We have found that the combination of Oxone with an organoiodine compound, i.e., 2-iodobenzoic acid (2-IB), selectively yields p-quinones from monomethoxyarenes under mild conditions. In this reaction system, an organoiodine compound is immediately oxidized by Oxone to generate cyclic hypervalent iodine (III) species in situ, which serves as the specific mediator for the selective p-quinone synthesis, preventing o-quinone formation.
Synthesis of coenzyme Q0 through divanadium-catalyzed oxidation of 3,4,5-trimethoxytoluene with hydrogen peroxide
Zalomaeva, Olga V.,Evtushok, Vasilii Yu.,Maksimov, Gennadii M.,Maksimovskaya, Raisa I.,Kholdeeva, Oxana A.
, p. 5202 - 5209 (2017/04/27)
The selective oxidation of methoxy/methyl-substituted arenes to the corresponding benzoquinones has been first realized using aqueous hydrogen peroxide as a green oxidant, acid tetrabutylammonium salts of the γ-Keggin divanadium-substituted phosphotungstate [γ-PW10O38V2(μ-O)2]5- (I) as a catalyst, and MeCN as a solvent. The presence of the dioxovanadium core in the catalyst is crucial for the catalytic performance. The reaction requires an acid co-catalyst or, alternatively, a highly protonated form of I can be prepared and employed. The industrially relevant oxidation of 3,4,5-trimethoxytoluene gives 2,3-dimethoxy-5-methyl-1,4-benzoquinone (ubiquinone 0 or coenzyme Q0, the key intermediate for coenzyme Q10 and other essential biologically active compounds) with 73% selectivity at 76% arene conversion. The catalyst retains its structure under turnover conditions and can be easily recycled and reused without significant loss of activity and selectivity.
A preparation method of idebenone (by machine translation)
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Paragraph 0020; 0023; 0025; 0027; 0029; 0031; 0033, (2017/09/01)
The invention relates to a preparation method of idebenone, the method comprises: to coenzyme Q0 and 11 - hydroxy undecanoic acid as the raw material, the choice of copper chloride, copper sulfate, copper acetate, silver carbonate, silver oxide, palladium chloride or palladium acetate in a metal salt as a catalyst, in the protection of the next adds oxygen oxidizing agent hydrogen peroxide, alkylation of the free radical reaction. The reaction system by extraction, water washing, drying, reduced pressure distillation, column chromatography, get the yellow needle-like crystal, 6 - (10 - hydroxyl decyl) - 2, 3 - dimethoxy - 5 - methyl - 1, 4 - benzoquinone, namely idebenone. This preparation method has a simple operation, low cost, and the yield and the like, suitable for large-scale industrial production of idebenone. (by machine translation)
Catalytic formation of hydrogen peroxide from coenzyme NADH and dioxygen with a water-soluble iridium complex and a ubiquinone coenzyme analogue
Suenobu, Tomoyoshi,Shibata, Satoshi,Fukuzumi, Shunichi
supporting information, p. 7747 - 7754 (2016/08/06)
A ubiquinone coenzyme analogue (Q0: 2,3-dimethoxy-5-methyl-1,4-benzoquinone) was reduced by coenzyme NADH to yield the corresponding reduced form of Q0 (Q0H2) in the presence of a catalytic amount of a [C,N] cyclometalated organoiridium complex (1: [IrIII(Cp?)(4-(1H-pyrazol-1-yl-κN2)benzoic acid-κC3)(H2O)]2SO4) in water at ambient temperature as observed in the respiratory chain complex I (Complex I). In the catalytic cycle, the reduction of 1 by NADH produces the corresponding iridium hydride complex that in turn reduces Q0 to produce Q0H2. Q0H2 reduced dioxygen to yield hydrogen peroxide (H2O2) under slightly basic conditions. Catalytic generation of H2O2 was made possible in the reaction of O2 with NADH as the functional expression of NADH oxidase in white blood cells utilizing the redox cycle of Q0 as well as 1 for the first time in a nonenzymatic homogeneous reaction system.
ONO-pincer ruthenium complex-bound norvaline for efficient catalytic oxidation of methoxybenzenes with hydrogen peroxide
Yoshida, Ryota,Isozaki, Katsuhiro,Yokoi, Tomoya,Yasuda, Nobuhiro,Sadakane, Koichiro,Iwamoto, Takahiro,Takaya, Hikaru,Nakamura, Masaharu
supporting information, p. 7468 - 7479 (2016/08/16)
The enhanced catalytic activity of ruthenium complex-bound norvaline Boc-l-[Ru]Nva-OMe 1, in which the ONO-pincer ruthenium complex Ru(pydc)(terpy) 2 is tethered to the α-side chain of norvaline, has been demonstrated for the oxidation of methoxybenzenes to p-benzoquinones with a wide scope of substrates and unique chemoselectivity.
